2-methyl-4H-isoquinoline-1,3-dione

反応条件: temp:125.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred mixture of 0.35 g (2.0 mmol) of (N-methyl)isoquinoline-1,3(2H,4H)-dione, 3.2 ml of Ac2O, and 0.80 ml of N,N-DIMETHYLFORMAMIDE (DMF) is added 0.44 ml (4.0 mmol) of (MeO)3CH at 25° C. The mixture is stirred at 125° C. for 30 m, cooled, and concentrated under high vacuum. The residue is recrystallized from Et2O-hexane to give 0.20 g of tan solid, mp 145-150° C. (dec); MS (ES+) m/z 218.2 (M+H)+1. cooled concentrated under high vacuum The residue is recrystallized from Et2O-hexane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2.28 g (11.8 mmol) of N-methyl-(2-carboxybenzeneacetamide and 24 ml of 1,2-dichlorobenzene is refluxed for 1 h and evaporated to dryness. The residue is recrystallized from EtOAc-hexane to give an off-white solid, 1.55 g (75%), mp 113-115° C.; MS (ES+) m/z 176.1 (M+H)+1. is refluxed for 1 h evaporated to dryness The residue is recrystallized from EtOAc-hexane to give an off-white solid, 1.55 g (75%), mp 113-115° C.

反応条件: temp:125.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred mixture of 0.35 g (2.0 mmol) of (N-methyl)isoquinoline-1,3(2H,4H)-dione, 3.2 ml of Ac2O, and 0.80 ml of N,N-DIMETHYLFORMAMIDE (DMF) is added 0.44 ml (4.0 mmol) of (MeO)3CH at 25° C. The mixture is stirred at 125° C. for 30 m, cooled, and concentrated under high vacuum. The residue is recrystallized from Et2O-hexane to give 0.20 g of tan solid, mp 145-150° C. (dec); MS (ES+) m/z 218.2 (M+H)+1. cooled concentrated under high vacuum The residue is recrystallized from Et2O-hexane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2.28 g (11.8 mmol) of N-methyl-(2-carboxybenzeneacetamide and 24 ml of 1,2-dichlorobenzene is refluxed for 1 h and evaporated to dryness. The residue is recrystallized from EtOAc-hexane to give an off-white solid, 1.55 g (75%), mp 113-115° C.; MS (ES+) m/z 176.1 (M+H)+1. is refluxed for 1 h evaporated to dryness The residue is recrystallized from EtOAc-hexane to give an off-white solid, 1.55 g (75%), mp 113-115° C.

反応条件: temp:125.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred mixture of 0.35 g (2.0 mmol) of (N-methyl)isoquinoline-1,3(2H,4H)-dione, 3.2 ml of Ac2O, and 0.80 ml of N,N-dimethylformamide is added 0.44 ml (4.0 mmol) of (MeO)3CH at 25° C. The mixture is stirred at 125° C. for 30 m, cooled, and concentrated under high vacuum. The residue is recrystallized from Et2O-hexane to give 0.20 g of tan solid, mp 145-150° C. (dec); MS (ES+) m/z 218.2 (M+H)+1: Analysis for C12H11NO3: Calcd: C, 66.35; H, 5.10; N, 6.45. Found: C, 65.98; H, 4.99; N, 6.42. cooled concentrated under high vacuum The residue is recrystallized from Et2O-hexane

反応条件: temp:125.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred mixture of 0.35 g (2.0 mmol) of (N-methyl)isoquinoline-1,3(2H,4H)-dione, 3.2 ml of Ac2O, and 0.80 ml of N,N-dimethylformamide is added 0.44 ml (4.0 mmol) of (MeO)3CH at 25° C. The mixture is stirred at 125° C. for 30 m, cooled, and concentrated under high vacuum. The residue is recrystallized from Et2O-hexane to give 0.20 g of tan solid, mp 145-150° C. (dec); MS (ES+) m/z 218.2 (M+H)+1: Analysis for C12H11NO3: Calcd: C, 66.35; H, 5.10; N, 6.45. Found: C, 65.98; H, 4.99; N, 6.42. cooled concentrated under high vacuum The residue is recrystallized from Et2O-hexane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2.28 g (11.8 mmol) of N-methyl-(2-carboxybenzeneacetamide and 24 ml of 1,2-dichlorobenzene is refluxed for 1 h and evaporated to dryness. The residue is recrystallized from EtOAc-hexane to give an off-white solid, 1.55 g (75%), mp 113-115° C.; MS (ES+) m/z 176.1 (M+H)+1. is refluxed for 1 h evaporated to dryness The residue is recrystallized from EtOAc-hexane to give an off-white solid, 1.55 g (75%), mp 113-115° C.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2.28 g (11.8 mmol) of N-methyl-(2-carboxybenzeneacetamide and 24 ml of 1,2-dichlorobenzene is refluxed for 1 h and evaporated to dryness. The residue is recrystallized from EtOAc-hexane to give an off-white solid, 1.55 g (75%), mp 113-115° C.; MS (ES+) m/z 176.1 (M+H)+1. is refluxed for 1 h evaporated to dryness The residue is recrystallized from EtOAc-hexane to give an off-white solid, 1.55 g (75%), mp 113-115° C.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2.28 g (11.8 mmol) of N-methyl-(2-carboxybenzeneacetamide and 24 ml of 1,2-dichlorobenzene is refluxed for 1 h and evaporated to dryness. The residue is recrystallized from EtOAc-hexane to give an off-white solid, 1.55 g (75%), mp 113-115° C.; MS (ES+) m/z 176.1 (M+H)+1. is refluxed for 1 h evaporated to dryness The residue is recrystallized from EtOAc-hexane to give an off-white solid, 1.55 g (75%), mp 113-115° C.

反応条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of N-methylhomophthalimide (4.05 kg), 1,2-dibromoethane (2.39 L), and Bu4NHSO4 (785 g) in N,N-dimethylformamide (32 L) were added K2CO3 (6.39 kg) and N,N-dimethylformamide (8.5 L) at room temperature. Then the solution was heated to 70° C., and was stirred for 2 hours at 68˜70° C. After cooling the reaction mixture to 40° C., water (81 L) was added. After the slurry was stirred for 1 hour at 40° C., it was allowed to cool to room temperature and was stirred overnight. The suspension was filtered, and the obtained wet crystal was washed with the mixture of N,N-dimethylformamide and water (N,N-dimethylformamide:water=1:1, 20 L), twice, and water (20 L), sequentially. It was dried at room temperature under N2 flow for several hours and then under the reduced pressure overnight to afford the title compound as pale pink crystal (4.67 kg, 4.30 kg assay, 92% yield). After cooling the reaction mixture to 40° C. After the slurry was stirred for 1 hour at 40° C. to cool to room temperature was stirred overnight The suspension was filtered the obtained wet crystal was washed with the mixture of N,N-dimethylformamide and water (N,N-dimethylformamide:water=1:1, 20 L) It was dried at room temperature under N2 flow for several hours

反応条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of N-methylhomophthalimide (4.05 kg), 1,2-dibromoethane (2.39 L), and Bu4NHSO4 (785 g) in N,N-dimethylformamide (32 L) were added K2CO3 (6.39 kg) and N,N-dimethylformamide (8.5 L) at room temperature. Then the solution was heated to 70° C., and was stirred for 2 hours at 68˜70° C. After cooling the reaction mixture to 40° C., water (81 L) was added. After the slurry was stirred for 1 hour at 40° C., it was allowed to cool to room temperature and was stirred overnight. The suspension was filtered, and the obtained wet crystal was washed with the mixture of N,N-dimethylformamide and water (N,N-dimethylformamide:water=1:1, 20 L), twice, and water (20 L), sequentially. It was dried at room temperature under N2 flow for several hours and then under the reduced pressure overnight to afford the title compound as pale pink crystal (4.67 kg, 4.30 kg assay, 92% yield). After cooling the reaction mixture to 40° C. After the slurry was stirred for 1 hour at 40° C. to cool to room temperature was stirred overnight The suspension was filtered the obtained wet crystal was washed with the mixture of N,N-dimethylformamide and water (N,N-dimethylformamide:water=1:1, 20 L) It was dried at room temperature under N2 flow for several hours